Title: Book the Best HISTORIC Hotels in Pittsfield in 2026 | Expedia.ca

[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d146411.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d146411.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d146411.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d146411.Destination-Travel-Guides)

![Court House in Pittsfield](https://images.trvl-media.com/place/146411/e1162892-98db-4e1f-aa10-c1e92fa5be83.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Historic Hotels in Pittsfield, IL from CA $122

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check availability on Pittsfield Historic Hotels

Tonight

[Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-12-21&endDate=2025-12-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pittsfield historic hotels

![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/6afc32c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, Ensuite (King Suite)](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/80a90a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/b7c49e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/23a03799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### William Watson Hotel

[](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information)

Pittsfield

9.2/10

Wonderful

(347)

"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Druann

CA $110

CA $122 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05&regionId=146411&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Pittsfield Hotel Reviews

![William Watson Hotel](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg)

### William Watson Hotel

10/10 Excellent

"Wonderful stay right on the town square with Christmas music playing. Felt a little like I was staying in Stars Hollow. Lovely people in this small town."

[](https://expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information)

## Frequently asked questions

### What should a history buff expect from a stay in Pittsfield?

### How many historical hotels are located in Pittsfield?

### What are the top historical places and other sights to visit in Pittsfield?

### What is a historic hotel like in Pittsfield?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Pittsfield have modern facilities?

## Explore a world of travel with Expedia

- Lodging
- Flights
- Packages
- Cars
- More ways to book

- [3 Star Hotels in Barry ](https://www.expedia.ca/3Star-Barry-Hotels.s30-0-d3000433380.Travel-Guide-Filter-Hotels)
- [Alsey Hotels ](https://www.expedia.ca/Alsey-Hotels.d3000346086.Travel-Guide-Hotels)
- [B&B in Atlas ](https://www.expedia.ca/Atlas-Bed-And-Breakfast.d3000346106-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Atlas ](https://www.expedia.ca/Atlas-Cabins.d3000346106-aaCabins.Travel-Guide-Accommodation)
- [Hotels with a Pool in Atlas ](https://www.expedia.ca/Atlas-Hotels-Hotel-With-Pool.0-0-d3000346106-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Atlas Hotels ](https://www.expedia.ca/Atlas-Hotels.d3000346106.Travel-Guide-Hotels)
- [Lodges in Atlas ](https://www.expedia.ca/Atlas-Lodges.d3000346106-aaLodges.Travel-Guide-Accommodation)
- [Motels in Atlas ](https://www.expedia.ca/Atlas-Motels.d3000346106-aaMotels.Travel-Guide-Accommodation)
- [Vacation Homes in Atlas ](https://www.expedia.ca/Atlas-Private-Vacation-Homes.d3000346106-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Farmstay in Barry ](https://www.expedia.ca/Barry-Agritourism.d3000433380-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Barry ](https://www.expedia.ca/Barry-Bed-And-Breakfast.d3000433380-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cheap Hotels in Barry ](https://www.expedia.ca/Barry-Hotels-Cheap-Hotels.0-0-d3000433380-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Barry ](https://www.expedia.ca/Barry-Hotels-Luxury-Hotel.0-0-d3000433380-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Barry Hotels ](https://www.expedia.ca/Barry-Hotels.d3000433380.Travel-Guide-Hotels)
- [Lodges in Barry ](https://www.expedia.ca/Barry-Lodges.d3000433380-aaLodges.Travel-Guide-Accommodation)
- [Motels in Barry ](https://www.expedia.ca/Barry-Motels.d3000433380-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Benville ](https://www.expedia.ca/Benville-Cabins.d553248635975847355-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Benville ](https://www.expedia.ca/Benville-Cottages.d553248635975847355-aaCottages.Travel-Guide-Accommodation)
- [Benville Hotels ](https://www.expedia.ca/Benville-Hotels.d553248635975847355.Travel-Guide-Hotels)
- [Cheap Hotels in Bluffs ](https://www.expedia.ca/Bluffs-Hotels-Cheap-Hotels.0-0-d553248634983410026-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Farmstay in Brown County ](https://www.expedia.ca/Brown-County-Agritourism.d553248635976433534-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Brown County ](https://www.expedia.ca/Brown-County-Motels.d553248635976433534-aaMotels.Travel-Guide-Accommodation)
- [Cheap Hotels in Carrollton ](https://www.expedia.ca/Carrollton-Hotels-Cheap-Hotels.0-0-d3000433678-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Carrollton ](https://www.expedia.ca/Carrollton-Hotels-Luxury-Hotel.0-0-d3000433678-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Cabin Rentals in Chapin ](https://www.expedia.ca/Chapin-Cabins.d553248634983501137-aaCabins.Travel-Guide-Accommodation)
- [Cheap Hotels in Concord ](https://www.expedia.ca/Concord-Hotels-Cheap-Hotels.0-0-d553248634983311133-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Brown County Hotels ](https://www.expedia.ca/Destinations-In-Brown-County.d553248635976433534.Hotel-Destinations)
- [Hotels & Resorts for Couples in Illinois ](https://www.expedia.ca/Destinations-In-Illinois-Couples-Resorts-Hotels.0-0-d215-tCouplesResortsHotels.Hotel-Filter-Destinations)
- [Hotels with Wifi in Illinois ](https://www.expedia.ca/Destinations-In-Illinois-Hotel-With-Wifi.0-0-d215-tHotelwithwifi.Hotel-Filter-Destinations)
- [Hotels with Free Airport Shuttle in Illinois ](https://www.expedia.ca/Destinations-In-Illinois-Hotels-With-Free-Airport-Shuttle.0-0-d215-tHotelswithFreeAirportShuttle.Hotel-Filter-Destinations)
- [Scuba Diving Hotels in Illinois ](https://www.expedia.ca/Destinations-In-Illinois-Scuba-Diving-Vacations.0-0-d215-tscubadivingvacations.Hotel-Filter-Destinations)
- [Winery Hotels in Illinois ](https://www.expedia.ca/Destinations-In-Illinois-Winery-Hotel.0-0-d215-tWineryHotel.Hotel-Filter-Destinations)
- [El Dara Hotels ](https://www.expedia.ca/El-Dara-Hotels.d553248634983342399.Travel-Guide-Hotels)
- [Cottages in Eldred ](https://www.expedia.ca/Eldred-Cottages.d100870-aaCottages.Travel-Guide-Accommodation)
- [Lodges in Exeter ](https://www.expedia.ca/Exeter-Lodges.d553248634983379267-aaLodges.Travel-Guide-Accommodation)
- [Lodges in Florence ](https://www.expedia.ca/Florence-Lodges.d553248634983143770-aaLodges.Travel-Guide-Accommodation)
- [B&B in Glasgow ](https://www.expedia.ca/Glasgow-Bed-And-Breakfast.d553248634983391345-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Hotels with a Pool in Glasgow ](https://www.expedia.ca/Glasgow-Hotels-Hotel-With-Pool.0-0-d553248634983391345-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Griggsville Hotels ](https://www.expedia.ca/Griggsville-Hotels.d3000346304.Travel-Guide-Hotels)
- [Vacation Homes in Hillview ](https://www.expedia.ca/Hillview-Private-Vacation-Homes.d553248634983096016-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Guest Houses in Hull ](https://www.expedia.ca/Hull-Guest-Houses.d553248634983347893-aaGuestHouses.Travel-Guide-Accommodation)
- [Historic Hotels in Jacksonville ](https://www.expedia.ca/Jacksonville-Hotels-Historic-Hotel.0-0-d7884-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Free Parking in Jacksonville ](https://www.expedia.ca/Jacksonville-Hotels-Hotels-With-Free-Parking.0-0-d7884-tHotelswithFreeParking.Travel-Guide-Filter-Hotels)
- [Hotels with Hot Tubs in Jacksonville ](https://www.expedia.ca/Jacksonville-Hotels-Hotels-With-Hot-Tubs.0-0-d7884-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Hotels with an Indoor Pool in Jacksonville ](https://www.expedia.ca/Jacksonville-Hotels-Hotels-With-Indoor-Pool.0-0-d7884-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
- [Lgbt Friendly Hotels in Jacksonville ](https://www.expedia.ca/Jacksonville-Hotels-LGBT-Friendly-Hotel.0-0-d7884-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Jacksonville ](https://www.expedia.ca/Jacksonville-Hotels-Luxury-Hotel.0-0-d7884-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Jacksonville ](https://www.expedia.ca/Jacksonville-Hotels-Pet-Friendly-Hotel.0-0-d7884-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Kampsville Hotels ](https://www.expedia.ca/Kampsville-Hotels.d553248634983209188.Travel-Guide-Hotels)
- [Cheap Hotels in La Prairie ](https://www.expedia.ca/La-Prairie-Hotels-Cheap-Hotels.0-0-d3000346370-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in La Prairie ](https://www.expedia.ca/La-Prairie-Hotels-Luxury-Hotel.0-0-d3000346370-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [B&B in Liberty ](https://www.expedia.ca/Liberty-Bed-And-Breakfast.d553248634983385377-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Lynnville Hotels ](https://www.expedia.ca/Lynnville-Hotels.d553248634983184392.Travel-Guide-Hotels)
- [B&B in Meredosia ](https://www.expedia.ca/Meredosia-Bed-And-Breakfast.d3000346427-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Meredosia Hotels ](https://www.expedia.ca/Meredosia-Hotels.d3000346427.Travel-Guide-Hotels)
- [Cheap Hotels in Mount Sterling ](https://www.expedia.ca/Mount-Sterling-Hotels-Cheap-Hotels.0-0-d553248634983461732-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Mozier Hotels ](https://www.expedia.ca/Mozier-Hotels.d3000346455.Travel-Guide-Hotels)
- [Naples Hotels ](https://www.expedia.ca/Naples-Hotels.d553248634983593506.Travel-Guide-Hotels)
- [B&B in Nebo ](https://www.expedia.ca/Nebo-Bed-And-Breakfast.d3000434627-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Nebo ](https://www.expedia.ca/Nebo-Cottages.d3000434627-aaCottages.Travel-Guide-Accommodation)
- [New Salem Hotels ](https://www.expedia.ca/New-Salem-Hotels.d553248634983461930.Travel-Guide-Hotels)
- [Hotels near Old Orchard Country Club ](https://www.expedia.ca/Old-Orchard-Country-Club-Hotels.0-l553248621564478943-0.Travel-Guide-Filter-Hotels)
- [Cottages in Pearl ](https://www.expedia.ca/Pearl-Cottages.d553248634983275112-aaCottages.Travel-Guide-Accommodation)
- [Pearl Hotels ](https://www.expedia.ca/Pearl-Hotels.d553248634983275112.Travel-Guide-Hotels)
- [Lodges in Pearl ](https://www.expedia.ca/Pearl-Lodges.d553248634983275112-aaLodges.Travel-Guide-Accommodation)
- [Cheap Hotels in Quincy ](https://www.expedia.ca/Quincy-Hotels-Cheap-Hotels.0-0-d3622-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Family Hotels in Quincy ](https://www.expedia.ca/Quincy-Hotels-Family-Hotel.0-0-d3622-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Quincy ](https://www.expedia.ca/Quincy-Hotels-Historic-Hotel.0-0-d3622-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Free Airport Shuttle in Quincy ](https://www.expedia.ca/Quincy-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d3622-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
- [Hotels with an Indoor Pool in Quincy ](https://www.expedia.ca/Quincy-Hotels-Hotels-With-Indoor-Pool.0-0-d3622-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Quincy ](https://www.expedia.ca/Quincy-Hotels-Luxury-Hotel.0-0-d3622-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Quincy ](https://www.expedia.ca/Quincy-Hotels-Pet-Friendly-Hotel.0-0-d3622-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Romantic Hotels in Quincy ](https://www.expedia.ca/Quincy-Hotels-Romantic-Hotel.0-0-d3622-tRomanticHotel.Travel-Guide-Filter-Hotels)
- [B&B in Rockport ](https://www.expedia.ca/Rockport-Bed-And-Breakfast.d3000435152-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cheap Hotels in Rockport ](https://www.expedia.ca/Rockport-Hotels-Cheap-Hotels.0-0-d3000435152-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Rockport ](https://www.expedia.ca/Rockport-Hotels-Luxury-Hotel.0-0-d3000435152-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Rockport Hotels ](https://www.expedia.ca/Rockport-Hotels.d3000435152.Travel-Guide-Hotels)
- [Inns in Rockport ](https://www.expedia.ca/Rockport-Inns.d3000435152-aaInns.Travel-Guide-Accommodation)
- [B&B in Roodhouse ](https://www.expedia.ca/Roodhouse-Bed-And-Breakfast.d3000346545-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Roodhouse ](https://www.expedia.ca/Roodhouse-Cottages.d3000346545-aaCottages.Travel-Guide-Accommodation)
- [Roodhouse Hotels ](https://www.expedia.ca/Roodhouse-Hotels.d3000346545.Travel-Guide-Hotels)
- [Cheap Hotels in Rushville ](https://www.expedia.ca/Rushville-Hotels-Cheap-Hotels.0-0-d3000435179-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels with a Pool in South Jacksonville ](https://www.expedia.ca/South-Jacksonville-Hotels-Hotel-With-Pool.0-0-d553248634983070122-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Valley City Hotels ](https://www.expedia.ca/Valley-City-Hotels.d553248634983409295.Travel-Guide-Hotels)
- [White Hall Hotels ](https://www.expedia.ca/White-Hall-Hotels.d553248634983416554.Travel-Guide-Hotels)
- [Vacation Homes in Wilmington ](https://www.expedia.ca/Wilmington-Private-Vacation-Homes.d553248634983100587-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://www.expedia.ca/Winchester-Bed-And-Breakfast.d3000435714-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Winchester Hotels ](https://www.expedia.ca/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)

- [Flights to Atlas ](https://www.expedia.ca/Cheap-Flights-To-Atlas.d3000346106.Travel-Guide-Flights)
- [Flights from Atlas ](https://www.expedia.ca/lp/flights/3000346106/flights-from-atlas)
- [Flights from Kampsville ](https://www.expedia.ca/lp/flights/553248634983209188/flights-from-kampsville)
- [Flights from Bluffs ](https://www.expedia.ca/lp/flights/553248634983410026/flights-from-bluffs)
- [Flights from Perry ](https://www.expedia.ca/lp/flights/553248634983586792/flights-from-perry)
- [Flights from Pike County ](https://www.expedia.ca/lp/flights/553248635976431336/flights-from-pike-county)

- [Atlas Vacations ](https://www.expedia.ca/Atlas.d3000346106.Destination-Travel-Guides)
- [Visit Atlas ](https://www.expedia.ca/Atlas.dx3000346106)
- [Visit Benville ](https://www.expedia.ca/Benville.dx553248635975847355)

- [Car rental Atlas ](https://www.expedia.ca/Car-Rentals-In-Atlas.d3000346106.Car-Rental-Guide)
- [Car rental Florence ](https://www.expedia.ca/Car-Rentals-In-Florence.d553248634983143770.Car-Rental-Guide)
- [Greenmotion Drive&Go Rental Cars in Griggsville ](https://www.expedia.ca/GreenMotion-DriveGo-Car-Rentals-In-Griggsville.d3000346304-c1042.Car-Rental-Guide-Suppliers)

- [Book Historic Hotels in Pittsfield on Expedia.com ](https://www.expedia.com/Pittsfield-Hotels-Historic-Hotel.0-0-d146411-tHistoricHotel.Travel-Guide-Filter-Hotels)